4-Aminobenzonitrile → 4-(4-Cyanophenyl)amino-2,6-dimethyl-3-nitropyridine

Participants

Reaction Steps

A solution of 4-chloro-2,6-dimethyl-3-nitropyridine (see part (b)) (9.80 g, 52.5 mmol) and 4-aminobenzonitrile (6.20 g, 52.5 mmol) in ethanol (160 ml) was stirred at room temperature for 16 hours. The solvent was removed under reduced pressure and the residue was dissolved in dichloromethane (200 ml) and washed with saturated aqueous sodium bicarbonate (100 ml). The organic phase was dried (MgSO4) and concentrated under reduced pressure to give a gum which was crystallised by adding ether (100 ml) and sonicating for 5 minutes. The title compound was obtained as a yellow solid which was filtered off and dried in vacuo, (9.80 g, 70%) m.p. 171°-172° C.

Provenance & Evidence